Methylamine ethanol → HCID 178431634, compound

HRID 1270000Notes

Reaction equation

HRID 1270000 reaction equation
[CH3:1][C:2]1[C:10]([O:11][C@@H:12]2[CH2:17][CH2:16][C@H:15]([N:18]3C(=O)C4C(=CC=CC=4)C3=O)[CH2:14][CH2:13]2)=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[N:5][N:6]2[CH:29]1[CH2:34][CH2:33][CH2:32][CH2:31][O:30]1.CN.C(O)C>>[CH3:1][C:2]1[C:10]([O:11][C@@H:12]2[CH2:13][CH2:14][C@H:15]([NH2:18])[CH2:16][CH2:17]2)=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[N:5][N:6]2[CH:29]1[CH2:34][CH2:33][CH2:32][CH2:31][O:30]1

Participants

3

Reactant 2

HCID 22028356Methylamine ethanolHCID 178431632HCID 178431632, compound

Product 1

HCID 178431634HCID 178431634, compoundYield 88.1%

Procedure

A mixture of 2-{cis-4-[(4-methyl-1-tetrahydro-2H-pyran-2-yl-1H-indazol-5-yl)oxy]cyclohexyl}-1H-isoindole-1,3(2H)-dione (95.5 mg, 0.208 mmol) and a 30% methylamine-ethanol solution (5.0 ml) was stirred with heating under reflux for 2 hours. The reaction solution was allowed to cool, and then was concentrated under reduced pressure to obtain a crude product. The crude product was purified by a silica gel column chromatography (eluent: chloroform/methanol/28% aqueous ammonia) to obtain cis-4-[(4-methyl-1-tetrahydro-2H-pyran-2-yl-1H-indazol-5-yl)oxy]cyclohexanamine (60.4 mg, 88%).

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for 2 hours
  3. temperatureto cool
  4. concentrationwas concentrated under reduced pressure
  5. customto obtain a crude product
  6. customThe crude product was purified by a silica gel column chromatography (eluent: chloroform/methanol/28% aqueous ammonia)

Sources & evidence

ORD record
ord-a390bf05b5a84b78aca4de183a2401b8
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

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